determination of four residues of fluoroquinolones with ... · determination of four residues of...
TRANSCRIPT
Int. J. Electrochem. Sci., 15 (2020) 6802 – 6814, doi: 10.20964/2020.07.55
International Journal of
ELECTROCHEMICAL SCIENCE
www.electrochemsci.org
Determination of Four Residues of Fluoroquinolones with
Similar Structure in Fish by Modified QuEChERS Protocol
Coupled to Capillary Electrophoresis (CE) with End-Column
Electrochemiluminescence (ECL)
Wenjuan Zhang1, Fuxiu Yang1, Hong Wang1, Chunxiu Gu1,2,*, Kaowen Zhou1,2,*
1Biochemical Engineering College, Beijing Union University, Beijing 100023, China 2Beijing Key Laboratory of Biomass Waste Resource Utilization, Beijing 100023, China *E-mail: [email protected], [email protected]
Received: 2 March 2020/ Accepted: 23 April 2020 / Published: 10 June 2020
A new method was established for simultaneousyl determining ciprofloxacin (CIP), enrofloxacin
(ENR), norfloxacin (NOR) and pefloxacin (PEF) in fish by capillary electrophoresis (CE) coupled with
end-column electrochemiluminescence (ECL) with modified QuEChERS. The structural differences of
4 FQs are too small to separate them by conventional CE. However, their separation efficiency can be
improved by adjusting the composition of separation buffer. The parameters about ECL analysis and
CE separation were investigated in detail. The use of methanol and sodium sulfate in QuEChERS can
improve the pretreatment effect of the sample. The optimum experimental conditions include analysis
conditions (detection potential 1.20 V vs. Ag/AgCl, Ru(bpy)32+ concentration 6 mmol/L, phosphate
buffer solution concentration 40 mmol/L and pH 7.0 in ECL detection cell), separation conditions
(separation voltage 13.0 kV, 17.5% cyclodextrin solution (v/v) as additive, phosphate buffer solution
concentration 20 mmol/L and pH 5.0 in capillary), and sample conditions (injection time 7 s and
injection voltage 12.0 kV). The limits of detection (3σ) of this method were 8.8×10-5 mg/mL for CIP,
3.5×10-6 mg/mL for ENR, 7.5×10-5 mg/mL for NOR and 2.7×10-6 mg/mL for PEF. The relative
standard deviations (RSD) were less than 2.6% for ECL intensity and less than 2.3% for migration
time. This method was successfully utilized to simultaneously determine CIP, ENR, NOR and PEF in
fish.
Keywords: Fluoroquinolones; Residue; Fish; CE-ECL; QuEChERS
1. INTRODUCTION
Fluoroquinolones (FQs) are a kind of important synthetic antibiotics, which are widely used in
the prevention and treatment of aquatic product diseases because of their broad antibacterial spectrum,
strong bactericidal power and convenient use [1,2]. However, improper and excessive use of these
Int. J. Electrochem. Sci., Vol. 15, 2020
6803
drugs will cause FQs residual pollution to aquatic products. Long term consumption of animal food
containing FQs residues will lead to drug resistance of pathogenic bacteria and indirectly affect human
health [3,4]. Therefore, it is very important to establish an efficient and sensitive method to detect FQs
residues in fish.
Numerous methods have been employed to analyze FQs residues, such as LC-MS [5-10],
fluorescence [11-15], electrophoresis [16-19], LC-UV [20-22], spectrophotometry [23] and
chemiluminescence [24]. Capillary electrophoresis (CE) is a promising high-performance biochemical
and medical separation method with short analysis time and less sample consumption. It has good
separation ability for molecules with similar structure. Electrochemiluminescence (ECL) based on tris
(2,2’-bipyridyl) ruthenium (II) (Ru (bpy)32+) is an attractive analytical method [25-27] for organic
amines owing to its high resolution, high sensitivity and high stability. CE separation couple with end-
column ECL analysis (CE-ECL) have been widely studied and used to analyze various drugs [28–36],
antibiotics [37], enzymes [38], alkaloids [39–41], amines [42], hormones [43] and pesticide residues
[44,45] in different foods, pharmaceuticals, animals and plants. FQs contain tertiary amino group
structure, and the molecular structure is similar. It is a good attempt to separate and analyze them with
CE-ECL.
The matrix of fish is complex, and the residual FQs are mostly in trace level. Sample
pretreatment technology has great influence on the sensitivity, efficiency and reliability of analytical
methods. The QuEChERS (quick, easy, cheap, effective, rugged and safe) is an efficient pretreatment
method based on dispersed solid phase extraction (SPE) [46], which integrates extraction and
purification. It has become the standard pretreatment method of American Association of Analytical
Chemists and European Standardization Committee. The QuEChERS method has many advantages,
such as short pretreatment time, simple operation and less amount of organic solvents. However, the
traditional QuEChERS method is mainly applied to substrates with more water content and less matrix
interference, such as vegetables and fruits [47-49]. The modified QuEChERS methods are based on the
specific improvement of complex substrates such as fish and poultry [50-53].
Among the FQs, ciprofloxacin (CIP), enrofloxacin (ENR), norfloxacin (NOR) and pefloxacin
(PEF) have little difference in molecular structure (see figure 1) [54]. It is challenging to separate and
analyze them. In this paper, the fish was treated with QuEChERS method, then CIP, ENR, NOR and
PEF were separated and detected simultaneously by overall optimization of CE-ECL conditions. The
results show that the present method is sensitive and reliable for the simultaneous determination of 4
residues of FQs with similar structure in fish.
N
OHF
N
HN
O O
N
OHF
N
N
O O
N
OHF
N
O O
HN
N
OHF
N
N
O O
CIP ENR NOR PEF
Figure 1. Structure of ciprofloxacin, enrofloxacin, norfloxacin and pefloxacin.
Int. J. Electrochem. Sci., Vol. 15, 2020
6804
2. EXPERIMENTAL
2.1. Materials and Reagents
Tris (2,2’-bipyridyl) ruthenium (II) dichloride hexahydrate (Ru(bpy)3Cl2·6H2O) was purchased
from Alfa Aesar (Johnson Matthey, USA). Disodium hydrogen phosphate (Na2HPO4), sodium
dihydrogen phosphate (NaH2PO4), ethyl acetate, acetonitrile, methanol, sodium hydroxide (NaOH),
anhydrous magnesium sulfate (MgSO4), anhydrous sodium sulfate (Na2SO4), primary secondary amine
(PSA), neutral alumina (NA), polyvinyl pyrrolidone, cyclodextrin, sodium dodecylsulfate, sodium
carboxymethyl cellulose, tween 80, n-propyl alcohol and iso-propyl alcoholwere all of analytical
reagent gradeand were purchased from Beijing Chemical Factory (Beijing, China). Standard
substances of ciprofloxacin (CIP), enrofloxacin (ENR), norfloxacin (NOR) and pefloxacin (PEF) were
purchased from National Institutes for Food and Drug Control (Beijing, China).
2.2. Apparatus
CE-ECL was performed on a MPI - B multi-parameter chemiluminescence analysis test system
(Xi’an Remex analytical instruments Co., Ltd., Xi’an, China). Cyclic voltammetry and potentiostatic
method were carried out in a three electrodes system with a platinum working electrode of 500 μm in
diameter, an Ag/AgCl reference electrode of 300 μm in diameter and a platinum wire auxiliary
electrode of 1 mm in diameter. Uncoated capillary (25μm x 40 cm, Yongnian Optical Fiber Factory,
Hebei, China) was rinsed respectively with 0.1 mol/L NaOH solution for 20 min, secondary distilled
water for 10 min and running buffer for 15 min before use.
2.3. Solutions preparation
Ru(bpy)32+solutions were prepared with Ru(bpy)3Cl2·6H2O and secondary distilled water.
Phosphate buffer solutions (PBS) were prepared with disodium hydrogen phosphate, sodium
dihydrogen phosphate and secondary distilled water. NaOH solution was prepared with NaOH and
secondary distilled water. Standard solutions of CIP, ENR, NOR and PEF were prepared with their
standard substances and secondary distilled water. All solutions used in the experiment must be filtered
through a 0.22 μm cellulose acetate membrane.
2.4. Sample preparation
Grass carp is fished from wild reservoirs in the suburbs. Feed with common fish food, and use
CIP, ENR, NOR and PEF for daily disease prevention. They will be slaughtered two months later. The
fish muscle was treated, homogenized and stored at −20 °C.
Accurately weigh 2.0 g of crushed homogeneous fish meat, put it in a 50 mL centrifugal tube
with cap, add 2 mL water, scroll for 1 min on the vortex oscillator, add 10 mL mixed solution of
acetonitrile and methanol (v/v=4/1), scroll for 1 min, place it on the ultrasonic oscillator for 20 min,
Int. J. Electrochem. Sci., Vol. 15, 2020
6805
scroll, put it in the ice water bath. Centrifuge at 5000 r/min for 5 min. Take 8 ml of supernatant into
another 15 ml centrifuge tube with cap. Add QuEChERS purification powder (0.4 g Na2SO4, 0.4 g NA
and 0.25 g PSA) into the centrifuge tube. The centrifuge tube was rotated for 1 minute and centrifuged
at 5000 r/min for 5 min. The supernatant was accurately removed, dried on a nitrogen blower at 50 ℃,
and dissolved in 1.0 ml methanol water (1:1). This sample preparation process is improved from our
original work [55]. After passing through 0.22 μm microporous membrane, the filter fluid can be
waiting for later use.
3. RESULTS AND DISCUSSION
3.1. Optimization of parameters in QuECHERS
The 4 FQs in this study belong to weak polar or medium polar compounds. The main extraction
reagents are ethyl acetate, acetonitrile or methanol. When ethyl acetate is used as extraction reagent,
the extract is darker in color, and more oily substances will remain after nitrogen blowing. It shows
that weak polar matrix components are brought out in the extraction process, which increases the
difficulty of subsequent purification. Acetonitrile has the function of protein precipitation, which can
reduce the matrix effect to some extent as reported in the literature [55]. In this experiment, the
recovery of FQs extracted by methanol is better than that of acetonitrile, but pure methanol as
extractant has subsequent salting-out effect. Through in-depth study, it is found that using
acetonitrile/methanol (v/v=4/1) mixture as extractant can not only ensure a good recovery of 4 FQs,
but also facilitate the follow-up treatment process. Therefore, the mixed solution of acetonitrile and
methanol (v/v=4/1) was used as the extraction reagent.
Most of the previous QuEChERS method used MgSO4 as the extraction salt to make the target
substance enter the organic phase [47-53]. In this experiment, however, the recoveries of 4 FQs were
poor by using MgSO4. This may be due to the chelation of FQs with Mg2+, which results in low target
recovery. The neutral Na2SO4, which does not react with FQs, was used as the extraction salt and good
recoveries were obtained. C18 and PSA are the most commonly used adsorbents, and their purification
effects are compared. The results show that PSA can not only remove carbohydrate and fatty acids
from the sample matrix, but also the recovery of analyte is much higher than that of C18. This
conclusion is also supported by the work of others from National Center for Biotechnology
Information [56]. In addition, NA can be combined with PSA to remove the fat in the sample solution.
Therefore, NA and PSA are adopted.
3.2. Optimization of detection conditions
3.2.1 Concentration of Ru(bpy)32+
Ru(bpy)32+ is the ECL reagent in the system. It is oxidized to Ru(bpy)3
3+ on the working
electrode [57], and then reacts with the reducing organic amine to produce the excited state product
[Ru(bpy)32+]*, which emits photons when it returns to the ground state [58]. It can be seen that the
initial concentration of Ru(bpy)32+ has an effect on the ECL intensity. The ECL intensity increased
Int. J. Electrochem. Sci., Vol. 15, 2020
6806
obviously with increasing the concentration of Ru(bpy)32+. The background signals, however,
increased markedly when its concentration exceeded 6 mmol/L. In order to obtain high S/N value, high
sensitivity and appropriate reagent consumption, 6 mmol/L Ru(bpy)32+ was selected. After working for
2 h, it is necessary to replace the Ru(bpy)32+ solution to eliminate the change of concentration of
Ru(bpy)32+ [59].
3.2.2 Detection potential
Figure 2. Effect of detection potential on ECL intensity under Ru(bpy)32+ concentration 6 mmol/L,
phosphate buffer solution concentration 40 mmol/L and pH 7.0 in ECL detection cell.
The effect of detection potential in the range of 0.80–1.30 V (vs. Ag/AgCl) on ECL intensities
of 5 mg/mL CIP、ENR、NOR and PEF under specific detection conditions was shown in figure 2. As
you can see, their ECL intensities were very weak when the detection potential is lower than 1.0 V,
because Ru(bpy)32+ can’t be oxidized at this potential [60]. The ECL intensities firstly increased and
then decreased with the detection potential from 1.00 V to 1.30 V. The ECL signals reached maximum
at 1.15-1.20 V for CIP and PEF and 1.20 V for ENR and NOR, respectively. Therefore, the detection
potential was set at 1.20 V (vs. Ag/AgCl) by comprehensive consideration.
3.2.3 pH of buffer in ECL cell
The effect of pH values of phosphate buffer solution (PBS) on ECL intensities of 5 mg/mL CIP、
ENR、NOR and PEF under specific detection conditions was shown in figure 3. The ECL intensities
increased with pH value from 4.0 to 6.5 and then decreased at higher pH value than 7.0. Because of be
Int. J. Electrochem. Sci., Vol. 15, 2020
6807
the competition of the reaction of Ru(bpy)33+ with OH− ions at higher pH values [61]. The maximum
ECL intensities appeared at pH 6.5-7.0 for CIP and PEF and 7.0 for ENR and NOR. Therefore, pH 7.0
of PBS can be used as the detection buffer.
Figure 3. Influence of pH of phosphate-buffer in ECL cell on ECL intensity under detection potential
1.20 V vs. Ag/AgCl, Ru(bpy)32+ concentration 6 mmol/L and phosphate buffer solution
concentration 40 mmol/L in ECL detection cell.
3.2.4 Concentration of PBS in ECL cell
Figure 4. Influence of concentration of phosphate-buffer in ECL cell on ECL intensity under detection
potential 1.20 V vs. Ag/AgCl, Ru(bpy)32+ concentration 6 mmol/L and phosphate buffer
solution pH 7.0 in ECL detection cell.
Int. J. Electrochem. Sci., Vol. 15, 2020
6808
The effect of concentration of PBS in the detection cell on ECL intensities of 5 mg/mL CIP、
ENR、NOR and PEF under specific detection conditions was shown in figure 4. As you can see, the
maximum ECL intensity appeared at 40-45 mmol/L for CIP and ENR and 40 mmol/L for NOR and
PEF. Therefore, the buffer concentration of 40 mmol/L was used as the detection buffer in our
experiment. Most of the concentrations of PBS reported in the literature are greater than 30 mmol/L
[25-27, 62].
3.3. Optimization of separation parameters
3.3.1 Selection of separation buffer
The only difference between CIP and ENR is that the nitrogen atom bonded to the hydrogen or
the ethyl groups. The only difference between NOR and PEF is that the nitrogen atom bonded to the
hydrogen or the methyl groups. The structure difference between them is too small to be separated by
general electrophoresis [63]. When there is no additive in the separation buffer, their electrophoretic
peaks overlap and cannot be separated. In order to obtain good resolution, the effect of
polyvinylpyrrolidone, cyclodextrin, sodium dodecylsulfate, sodium carboxymethyl cellulose, Tween
80, n-propyl alcohol and iso-propyl alcohol on their separation were studied by adding them into the
separation buffer, respectively. The results showed that polyvinylpyrrolidone, n-propyl alcohol and
iso-propyl alcohol had obvious influence on the separation of CIP and ENR, sodium dodecylsulfate
and sodium carboxymethyl cellulose had obvious influence on the separation of NOR and PEF, and
cyclodextrin and Tween 80 had great influence on the separation of CIP、ENR、NOR and PEF.
Cyclodextrin is especially effective in improving their separation. The influence of cyclodextrin
volume fraction in separation buffer on separation was further studied. The results showed that 4 FGs
could be separated completely when the volume fraction of cyclodextrin in separation buffer was
17.5%. In following experiments, 17.5% cyclodextrin solution (v/v) containing phosphate was used as
the separation buffer.
3.3.2 Injection voltage and injection time
The amount of capillary electric injection is directly related to the injection voltage and
injection time [60]. The effects of injection voltage from 4-20 kV on the ECL intensities of 4 FGs were
studied by fixing the injection time at 10 s. The results show that the ECL intensities of the four
molecules increase sharply before 11 kV with the increase of injection voltage, then slowly, and the
reproducibility deteriorate gradually after 15 kV. The effects of inject time from 2-20 s on the ECL
intensities of 4 FGs were studied by fixing the injection voltage at12 kV. The results show that the
ECL intensities increase sharply for 4 FGs before 6 s with the injection time, and then slowly for them.
However, due to the introduction of more analytes into the capillary and overload may occur, so a
longer injection time is unfavorable [59]. Therefore, 6-10 s and 11-15 kV are selected by considering
signal sensitivity and separation efficiency together.
Int. J. Electrochem. Sci., Vol. 15, 2020
6809
3.3.3 Separation voltage
The separation voltage has a great influence on the separation of four FGs [61]. We have
studied the relationship between them in the range of 8–20 kV. For all of them, ECL intensities
increased with separation voltage from 8 to 14 kV, and then they slowly decreased from 14 to 20 kV.
The baseline noise significant increase when the separation voltage was higher than 14 kV. On the one
hand, the Joule heat increased with the increase of separation voltage which will make the noise
enlarge. On the other hand, the more effluent from the capillary, the lower concentration of
Ru(bpy)32+ on the electrode surface [60]. That will reduce the efficiency of light emitting. To obtain a
high ECL intensity and high resolution, lower separation voltage than 14 kV is necessary.
3.3.4 The pH of separation buffer and concentration of phosphate
The pH value of the separation buffer and concentration of phosphate can affect the electro
osmotic flow (EOF) and ionization degree of the analytes in the capillary, and then affect the migration
time, sensitivity and resolution of the analytes [60]. The results showed that when the pH value was
more than 6, the four FGS could not be separated completely in electropherogram, the resolution was
not improved with the increasing of concentration of phosphate from 5–22 mmol/L, and the bad
separation effect, long migration time and unstable baseline appeared when its concentrations was
higher than 22 mmol/L. This may be due to the increase of Joule heating caused by the increase of
ionic strength. This phenomenon is also supported by literature work [64]. In order to obtain ideal
separation and short migrating time, smaller buffer pH than 6 and lower buffer concentration than 22
mmol/L are necessary.
3.3.5 Separation conditions
When multi-components are simultaneously determined, the overall optimization of separation
conditions is particularly important [55]. The experimental results show that the migration times and
the peak profiles are the main factors of influencing the separation of components. The migration time
mainly depends on the electrophoresis ionic strength and the separation voltage. The electrophoresis
ion strength can be appropriately changed by adjusting the concentration and pH value of the buffer
solution. The component peak profile is related to the sampling volume and the migration time of the
component. The sampling volume can be changed by adjusting the injection voltage and injection time.
Although the long migration time is beneficial to the separation of components, it is easy to cause the
peak broadened and the column effect decreased. Considering these conditions, the electrophoresis
separation diagram of a mixed solution comprising 4 FGs (see figure 5) was obtained through a large
number of comprehensive optimization experiments. The separation conditions were determined:
separation buffer of 17.5% cyclodextrin solution (v/v) containing 20 mmol/L phosphate (pH 5.0),
separation voltage of 13.0 kV, sample injection time of 7 s and sample injection voltage of 12.0 kV. It
can be seen that 4 FGs can be completely separated under these conditions.
Int. J. Electrochem. Sci., Vol. 15, 2020
6810
Figure 5. Electrophoretogram of mixture of 4 standard FGs under analysis potential 1.20 V,
Ru(bpy)32+ concentration 6 mmol/L, phosphate buffer solution concentration 40 mmol/L and
pH 7.0 in ECL detection cell, separation voltage 13.0 kV, 17.5% cyclodextrin solution (v/v) as
additive, phosphate buffer solution concentration 20 mmol/L and pH 5.0 in capillary, and
injection time 7 s and injection voltage 12.0 kV.
3.4 Method performances
The optimized CE–ECL experimental conditions include analysis conditions (detection
potential 1.20 V vs. Ag/AgCl, Ru(bpy)32+ concentration 6 mmol/L, phosphate buffer solution
concentration 40 mmol/L and pH 7.0 in ECL detection cell), separation conditions (separation voltage
13.0 kV, 17.5% cyclodextrin solution (v/v) as additive, phosphate buffer solution concentration 20
mmol/L and pH 5.0 in capillary), and sample conditions (injection time 7 s and injection voltage 12.0
kV). Under the optimal conditions, the analytical results of 4 FGs were summarized in Table1.
Table 1. Regression equation, repeatability and detection limit of four analytes.
Drug Regression Equation Linear Range/(g/L) RSDI/% RSDt/% Detection Limit/(g/L)
CIP I = 251.5C+ 52.8 2.5×10-4~4.9×102 2.6 1.7 8.8×10-5
ENR I = 226.8C+ 106.3 7.1×10-5~6.0×103 1.8 2.1 3.5×10-6
NOR I = 305.3C+76.6 8.8×10-4~6.2 ×102 1.6 1.9 7.5×10-5
PEF I = 279.7C+ 82.1 5.4×10-5~7.7×103 2.3 2.3 2.7×10-6
* I: ECL intensity. C: mass concentration. RSDI: RSD of ECL intensity. RSDt: RSD of migration time.
Int. J. Electrochem. Sci., Vol. 15, 2020
6811
3.5 Sample analysis
The filtrate of grass carp treated by modified QuEChERS was directly separated and analyzed
by CE-ECL under the optimal conditions. The results are shown in figure 6. The component peaks
appeared more in figure 6 than in figure 5. This indicates that not only 4 FGs, but also other
components are detected simultaneously.
Figure 6. Electrophoretogram of fish sample original liquid under analysis potential 1.20 V,
Ru(bpy)32+ concentration 6 mmol/L, phosphate buffer solution concentration 40 mmol/L and
pH 7.0 in ECL detection cell, separation voltage 13.0 kV, 17.5% cyclodextrin solution (v/v) as
additive, phosphate buffer solution concentration 20 mmol/L and pH 5.0 in capillary, and
injection time 7 s and injection voltage 12.0 kV.
In order to further determine the peak location of the target, the CE - ECL measurement of a
mixture solution of containing 1 ml standard solution (5 mg/mL CIP, 5 mg/mL ENR, 4 mg/mL NOR,
and 4 mg/mL PEF) and 5 ml the filtrate of grass carp sample was performed under the optimal
conditions. The results were shown in figure 7.
Compared with figure 6, the luminescence intensity of the four peaks in figure 7 is significantly
increased, which can accurately determine the location of CIP, ENR, NOR and PEF.
Int. J. Electrochem. Sci., Vol. 15, 2020
6812
Figure 7. Electrophoretogram of fish sample spiked with standards under analysis potential 1.20 V,
Ru(bpy)32+ concentration 6 mmol/L, phosphate buffer solution concentration 40 mmol/L and
pH 7.0 in ECL detection cell, separation voltage 13.0 kV, 17.5% cyclodextrin solution (v/v) as
additive, phosphate buffer solution concentration 20 mmol/L and pH 5.0 in capillary, and
injection time 7 s and injection voltage 12.0 kV.
4.CONCLUSION
This paper firstly demonstrated an analytical procedure for simultaneous determination of CIP,
ENR, NOR and PEF by improved CE coupled with end-column ECL and modified QuEChERS. The
four analytes with similar structure can be separated and analyzed well in less than 12 minutes by
comprehensive optimization of CE-ECL conditions. It was successfully utilized to directly
simultaneously detect CIP, ENR, NOR and PEF in fish sample.
ACKNOWLEDGEMENTS
This work was supported by Beijing Natural Science Foundation of China (Grant No.2152013) and
State 863 Program of China (2015AA020200).
References
1. C. Song, C. Zhang, B. Kamira, L. Qiu, L. Fan, W. Wu, S. Meng, G. Hu and J. Chen, Environ.
Toxicol. Chem., 36 (2017) 2899-2905.
2. P. Aleksei,T. Irina, V. Christina, B. Andrey, Anal. Chim. Acta, 976 (2017) 35-44.
3. S. Liu, G. Dong, H. Zhao, M. Chen, W. Quan and B. Qu, Environ. Sci. Pollut. R., 25 (2018) 8035-
8043.
4. M. Wagil, J. Kumirska, S. Stolte, A. Puckowski, J. Maszkowska, P. Stepnowski and A. Bialk-
Bielinska, Sci. Total Environ., 493 (2014) 1006-1013.
5. Y. Chen, S. Xia, X. Han and Z. Fu, J. Anal. Methods Chem., 2020 (2020) Article ID 3725618.
Int. J. Electrochem. Sci., Vol. 15, 2020
6813
6. Y. Tang, J. Xu, Le Chen, J. Qiu, Y. Liu and G. Ouyang, Talanta, 175 (2017) 550-556.
7. H. Ziarrusta, N. Val, H. Dominguez, L. Mijangos, A. Prieto, A. Usobiaga, N. Etxebarria, O.
Zuloaga and M. Olivares, Anal. Bioanal. Chem., 409 (2017) 6359-6370.
8. J.M. Storey, S.B. Clark, A.S. Johnson, W.C. Andersen, S.B. Turnipseed, J.J. Lohne, R.J. Burger,
P.R. Ayres, J.R. Carr and M.R. Madson, J. Chromatogr. B, 972 (2014) 38-47.
9. P.S. Peixoto, I.V. Toth, L. Barreiros, A. Machado, A.A. Bordalo, J.L.F.C. Lima and M.A. Segundo,
Int. J. Environ. An. Ch., 99 (2019) 258-269.
10. H. Yu, Y. Jia, R. Wu, X. Chen and T.D. Chan, Anal. Bioanal. Chem., 411 (2019) 2817-2826.
11. A. Osorio, C. Toledo-Neira and M.A. Bravo, Talanta, 204 (2019) 438-445.
12. J. Aufartova, I. Brabcova, M.E. Torres-Padron, P. Solich, Z. Sosa-Ferrera and J.J. Santana-
Rodriguez, J. Food Compos. Anal., 56 (2017) 140-146.
13. S.S. Bozkurt, D. Erdogan, M. Antep, N. Tuzmen and M. Merdivan, J. Liq. Chromatogr. R. T., 39
(2016) 21-29.
14. Y. Ouyang, H. Wu, H. Fang, T. Wang, X. Sun, Y. Chang, Y. Ding and R. Yu, Spectrochim. Acta A,
224 (2020) 117458.
15. M. Rizk, I.H.I. Habib, D. Mohamed, S. Mowaka and R.T. El-Eryan, Microchem. J., 150 (2019)
104138.
16. Y. Deng, N. Gasilova, L. Qiao, Y. Zhou, X. Zhang and H.H. Girault, Electrophoresis, 35 (2014)
3355-3362.
17. V. Springer, J. Jacksen, P. Ek, A.G. Lista and A. Emmer, J. Sep. Sci., 37 (2014) 158-164.
18. D. Li, Q. Yang, Z. Wang, R. Su, X. Xu and H. Zhang, J. Sep. Sci., 34 (2011) 822-829.
19. H. Sun, Y. Zuo, H. Qi and Y. Lv, Anal. Methods-UK, 4 (2012) 670-675.
20. B. Zhao, H. Wu, Y. Liu, X. Tian, Y. Huo and S. Guan, Anal. Methods-UK, 11 (2019) 1491-1499.
21. H. Wu, Y. Liu, J. Chang, B. Zhao, Y. Huo, Z. Wang and Y. Shi, Food Anal. Method., 12 (2019) 712-
721.
22. P. Moudgil, J.S. Bedi, R.S. Aulakh, J.P.S. Gill and A. Kumar, Food Anal. Method., 12 (2019) 338-
346.
23. D.N. Trung, B.L. Hoc, O.D. Thi and D.P. Tien, J. Anal. Methods Chem. 2018 (2018) 8436948.
24. J. Li, S. Lu, J. Xiang, X. Xu, L. Wei and X. Cheng, Food Chem., 298 (2019) UNSP 125066.
25. W.J. Miao, Chem. Rev., 108 (2008) 2506-2553.
26. G.M. Zhu, S.H. Long, H. Sun, W. Luo, X. Li, Z.B. Hao, J. chromatogr. B, 941 (2013) 62-68.
27. Y.C. Wang, Q. Wu, M.R. Cheng, C. Cai, J. chromatogr. B, 879 (2011) 871-877.
28. S.J. Sun, Y.F. Wei,H. Wang,Y.P. Cao, B.Y. Deng, Talanta, 179 (2018) 213-220.
29. R.N. Wei, Z.Y. Chen, J.Z. Geng, Mod. Food Sci. Tech., 33 (2017) 257-263.
30. S.J. Sun, Y.F. Wei, Y.P. Cao, B.Y. Deng, J. Chromatogr. B,1055-1056 (2017) 15-19.
31. Y.F. Wei, H. Wang, S.J. Sun, L.F. Tang, Y.P. Cao, B.Y. Deng, Biosens.Bioelectron., 86 (2016) 714-
719.
32. Y. Dong, E.B. Liu, Asian J. Chem., 28 (2016) 1239-1243.
33. S.J. Sun, Y.F. Wei, C.J. Long,B.Y. Deng,J. Chromatogr. B,1006 (2015) 146-150.
34. M. Zuo, J.Y. Gao, X.Q. Zhang, Y. Cui, Z.M. Fan, M. Ding, J. Sep. Sci., 38 (2015) 2332-2339.
35. H.B.Duan, J.T. Cao, H. Wang, Y.M. Liu, Anal. Methods, 7 (2015) 3946-3951.
36. H.J. Zeng, R. Yang, Y. Zhang, J.J. Li, L.B. Qu, Luminescence, 30 (2015) 124-130.
37. C.J. Long, B.Y. Deng, S.J. Sun, S. Meng, Food Addit.Contam., 34 (2017), 24-31.
38. D.D. Wang, F.L. Li, M. Su, H.W. Sun, J. Appl. Pharm. Sci., 8 (2018) 7-14.
39. H. Guo, X.L. Wu, A.L. Wang, X.W. Luo, Y.J. Ma,M. Zhou, New J. Chem., 39 (2015) 8922-8927.
40. Q.W. Zhou, D. Wu, Q. Meng, H.B. Tang, Z.R. Wei, Y. Kuang, J.Y. Yin, J.J. Chen, Anal. Sci., 29
(2013) 757-760.
41. Q. Xiang, Y. Gao, B.Y. Han, J. Li, Y.H. Xu, J.Y. Yin, Luminescence, 28 (2013) 50-55.
42. D. An, Z.Q. Chen, J.C. Zheng, S.Y. Chen, L. Wang, Z.Y. Huang, L. Weng, Food Chem., 168 (2015)
1-6.
Int. J. Electrochem. Sci., Vol. 15, 2020
6814
43. Y.Y. Hu, X.P. Wei, Curr. Anal. Chem., 14 (2018) 504-511.
44. Y.F. Hu, J.Chromatogr. B, 986-987 (2015) 143-148.
45. C. Cai, H.Y. Cheng, Y.C. Wang, Anal. Methods, 6 (2014) 2767-2773.
46. N.B. Turan, E. Maltepe, D.S. Chormey and S. Bakirdere, Environ. Monit. Assess., 192 (2020)
RA141-RA147.
47. M. Ana, S.V.M. Morales, L.G. Agustin, P. Yolanda, Anal. Chim. acta, 936 (2016) 40-61.
48. V.C. Fernandes, M. Freitas, J.G. Pacheco, V.F. Domingues and C. Delerue-Matos, Food Chem.,
309 (2020) 125572.
49. D.B. Alcantara, T.S.M. Fernandes, H.O. Nascimento, A.F. Lopes, M.G.G. Menezes, A.C.A. Lima,
T.V. Carvalho, P. Grinberg, M.A.L. Milhome, A.H.B. Oliveira, H. Becker, G.J. Zocolo and R.F.
Nascimento, Food Chem., 298 (2019) UNSP 124958.
50. S. Mandal, R. Poi, S. Bhattacharyya, I. Ansary, S.D. Roy, D.K. Hazra and R. Karmakar, J. Aoac
Int., 103 (2020) 62-67.
51. M.G. Melo, A. Carqueijo, A. Freitas, J. Barbosa and A.S. Silva, FOODS, 9 (2020)
WOS:000513235300018.
52. S. Chevolleau, A. Bouville and L. Debrauwer, Food Chem., 316 (2020) 126327.
53. Y. Wu, L. Chen, Y. Xian, X. Hou, M. Liang, H. Dong and J. Chen, Food Chem., 298 (2019) 125048.
54. J.P. Wang, J. Dong, C.F. Duan, H.C. Zhang, X. He, G.N. Wang, G.X. Zhao, J. Liu, J. Agric. Food
Chem., 64 (2016) 7957-7965.
55. C.X. Gu, Y.L. Cheng, X. Zhen, X.X. Chen and K.W. Zhou, J. Anal. Methods Chem., 2019 (2019)
Article ID 6426958.
56. www.ncbi.nlm.nih.gov
57. X.J. Zou, F. Shang, S. Wang, Spectrochim. Acta A, 173 (2017) 843-848.
58. M.S.Burkhead, H.Y. Wang, M. Fallet, E.M. Gross, Anal. Chim. Acta, 613 (2008) 152-162.
59. Z.L. Zhang, J.J. Li, L.B. Qu, R. Yang, Chinese J. Anal. Chem., 36 (2008) 941-946.
60. Y.H Li, C.Y. Wang, J.Y. Sun, Y.C. Zhou, T.Y. You, E.K. Wang and Y.S. Fung, Anal. Chim. Acta,
550 (2005) 40-46.
61. C.X. Yu, H.W. Du, T.Y. You, Talanta, 83 (2011) 1376-1380.
62. B.Q. Yuan, J.S. Huang, J.Y. Sun, T.Y. You, Electrophoresis, 30 (2009) 479-486.
63. S.J. Sun, Y.F. Wei, H. Wang, Y.P. Cao, B.Y. Deng, Talanta, 179 (2018) 213-220.
64. L. Xu, L.B. Li, J.S. Huang, T.Y. You, Talanta, 118 (2014) 1-6.
© 2020 The Authors. Published by ESG (www.electrochemsci.org). This article is an open access
article distributed under the terms and conditions of the Creative Commons Attribution license
(http://creativecommons.org/licenses/by/4.0/).